m-Chloroperbenzoic acid → 6-cyano-2-(2-ethylsulfinylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine

HRID 923752Notes

Reaction equation

HRID 923752 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[S:18][CH2:19][CH3:20])[N:9]([CH3:21])[C:6]2=[N:7][CH:8]=1)#[N:2].ClC1C=CC=C(C(OO)=[O:30])C=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[S:18]([CH2:19][CH3:20])=[O:30])[N:9]([CH3:21])[C:6]2=[N:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 867082066-cyano-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 867082076-cyano-2-(2-ethylsulfinylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridineYield 94.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 6-cyano-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (0.40 g) and chloroform (5 ml), 70% of 3-chloroperbenzoic acid (0.35 g) was added under ice-cooling, and stirred at room temperature for 2 hours. To the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 0.40 g of 6-cyano-2-(2-ethylsulfinylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 49).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-368eef9d0954465cbb1059610a65101d
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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